







About Jonathan
A lifelong resident of the Boothbay Peninsula, Jonathan’s travel to all 48 contiguous states has heightened his appreciation for the Boothbay Region. Jonathan is proud of its beautiful landscape, tight-knit community, and recreational offerings. In an effort to “give back”, Jonathan volunteers in his community; Jonathan is past president of the boards of the Boothbay Region YMCA and Rotary Club, former Land Trust board member, and a Lieutenant of the Boothbay Fire Department. During his free time, Jonathan enjoys boating, tennis, the great outdoors, family, and friends. Jonathan, his wife, Jessica, and their daughters, Olivia and Cora, live in Boothbay near Ovens Mouth; it is a place they are thrilled to call “home”.
Transaction History
- 1 Year
- 2 Year
- 5 Year
Seller Deals
Buyer Deals
Production Over Time
1 Year View by Quarter
Seller Deals
Buyer Deals
Production Over Time
2 Year View by Quarter
Seller Deals
Buyer Deals
Production Over Time
5 Year View
Jonathan's Listings and Deals
Jonathan's Recent Active Listings
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$795,000
- Land
- 2.27 Acres
- $350,220 per Acre
- Lot 2 Osprey Landing Dr
- Southport, ME
This Southport Island building lot offers commanding views of Boothbay Harbor's boating activity and islands, with a long and elevated perspective. At the shore, its 150' (tie) deep water frontage encourages convenient and protected water access for boaters. Less than a mile from the bridge to Boothbay Harbor, this location delivers the charm of Southport living with quick access to all of the
Jonathan Tindal Tindal & Callahan Real Estate
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$795,000
- Land
- 2.1 Acres
- $378,571 per Acre
- Lot 3 Osprey Landing Dr
- Southport, ME
This Southport Island building lot offers a building site close to the shore, with leisurely access to its 150' (tie) deep water frontage. Views will include all of Boothbay Harbor's boating activity, plus that of a small, nearby marina. An excellent location for boaters, and/or those seeking Southport's renowned community, coastal charm, and low property taxes.
Jonathan Tindal Tindal & Callahan Real Estate
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$2,795,000
- 4 Beds
- 4.5 Baths
- 5,874 Sq Ft
- 50 Higbee Ln
- Boothbay, ME
A private retreat in a tranquil setting, this 4+ bedroom, 4.5-bath home on 5+ acres delivers the ultimate in waterfront satisfaction. Family gatherings are encouraged here, with spacious indoor and outdoor living spaces, including an open concept marble kitchen to living room, large decks and a screened porch, a family room with kitchenette, grounds for lawn games and bonfires, and multiple
Jonathan Tindal Tindal & Callahan Real Estate
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$1,050,000
- 4 Beds
- 2 Baths
- 1,150 Sq Ft
- 16 Tilton Ln
- Southport, ME
Located off the east shore of Southport Island, and connected by bridge, Capitol Island is an old-time cottage community, rich with social and recreational opportunities. Perched on a rocky point of land with southerly exposure, this 4BR/2BA classic cottage enjoys marvelous views of Boothbay Harbor's boating activity and outer islands, and is well-positioned to receive the prevailing summertime
Jonathan Tindal Tindal & Callahan Real Estate
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$1,150,000
- 1 Bed
- 1 Bath
- 1,300 Sq Ft
- 32 Murray Hill Rd
- Boothbay, ME
Imagine the charm of Old World with all the modern conveniences of today. This amazing Carriage House was totally renovated in 2021 without giving up its soul. Drenching light, from sunrise to sunset, through immense french doors with views of a five acre Marsh Pond and Island across ten acres of open meadow protected by a conservation trust. The open floor plan encompasses a custom kitchen,
Jonathan Tindal Tindal & Callahan Real Estate
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$725,000
- 4 Beds
- 3 Baths
- 2,156 Sq Ft
- 58 Hendricks Hill Rd
- Southport, ME
On Southport Island, this turn-key property features many recent improvements in a convenient location. The 4-bedroom, 3-bathroom home includes optional one-floor living, Vermont Castings wood stove, covered porch & open deck, granite kitchen, etc.. Fundamental improvements include connection to town water, a 2020 septic, 2021 roof, 2021 automatic generator, paved driveway, gardens & hardscape,
Jonathan Tindal Tindal & Callahan Real Estate
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$650,000
- 3 Baths
- 2,198 Sq Ft
- 9 School St
- Boothbay Harbor, ME
On a quiet, one-way street at the head of Boothbay Harbor, this three unit property is tucked away, yet close to all of the action of this quintessential coastal Maine town. Built around 1830, it has charming character and style, and offers many possibilities for future use, including short-term and year-round rentals, owner occupancy with rental income, staff housing, and more. Unit A enjoys
Jonathan Tindal Tindal & Callahan Real Estate
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$650,000
- 5 Beds
- 3 Baths
- 2,198 Sq Ft
- 9 School St
- Boothbay Harbor, ME
On a quiet, one-way street at the head of Boothbay Harbor, this three unit property is tucked away, yet close to all of the action of this quintessential coastal Maine town. Built around 1830, it has charming character and style, and offers many possibilities for future use, including short-term and year-round rentals, owner occupancy with rental income, staff housing, and more. Unit A enjoys
Jonathan Tindal Tindal & Callahan Real Estate
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$489,000
- 3 Baths
- 1,858 Sq Ft
- 934 Wiscasset Rd
- Boothbay, ME
On 1.25-acres at the gateway to the Boothbay Region, this two-unit New Englander offers many possibilities in a mixed-use zoning district. Both units were recently updated, including the kitchens, bathrooms, flooring, and more. The first floor features a spacious 1-bedroom, 2-bath apartment, with vaulted ceilings and a propane heat stove in the living room, a cheerful kitchen with adjacent
Jonathan Tindal Tindal & Callahan Real Estate

